This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This file focusses on letters written or received by Walter Lee Sargant.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

A letter from O.O. Alwyne Westmoreland to the Headmaster, John Buchanan, regarding Oakham School winning the Ashburton Shield, captained by Chris Frame, in 1966.

A letter from Beatrice Townrow thanking David Morgan and the boys for taking photographs of the Queen's visit on Doncaster Close.

A letter from Alwyne Westmoreland to the Headmaster, John Buchanan, apologizing for not being able to participate in the next Development Campaign. Two pages A and B.

A bound copy of several Old Oakhamian Magazines from 1974 to 1979.

The Old Oakhamian Magazine, published in 1976. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; J.W. and H.Y.H.; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Change of Address; Masonic Lodge; Notices; Diary Dates; Golf. Seventeen double-pages A to Q.

A letter from john Barber to Brian Welford regarding an Old Oakhamian, Radu Nicolas Tabacavici ('31) who played in the 1st XV.

A letter from David Loveday, Chairman of the 1993 Oakham Festival, to Roger Blackmore regarding his role to spear-head the publicity side of Oakham Festival.